How to talk to a tailor

Monday, September 12th 2016
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I get nervous talking to tailors.

Not to stumble or stutter, but there will always be a point where I want to bring something up, and hesitate.

Being in tailor's is intimidating, whether on Savile Row or not. In fact most shops can be intimidating - you often feel ill-at-ease, slightly dreading the inevitable 'can I help you?' inquiry.

(There is a trend at the moment in restaurants for waiters to behave more like people, less like servants. Less formality; more just helpfulness and politeness. I wish there were more of that.)

Perhaps most surprisingly, talking to a tailor/shoemaker/shirtmaker can be nerve-wracking even when it's someone you know well, after years of custom.

There are several reasons for this.

One, you are often asked for your opinion on something you are not entirely sure about (doubtless a reason many read this blog).

Two, the things you might bring up are often critical, and therefore awkward.

And three, there is a sharp asymmetry of knowledge: he is a master craftsman, you are not. (And on the flip side, you have spent hours looking at suit styles from around the world; he has not.)

It is important to try to get over this, because communication is key in any bespoke appointment.

A tailor cannot know your presumptions of style; a shoemaker cannot know how you like your shoes to fit.


I have failed to communicate effectively on several occasions in the past, and always regretted it. I'm a lot better now, but there are few things I always try to remember.

First, be polite and respectful. Even if you think something is hilariously outdated, or plain wrong, express your point with respect. This may seem obvious, but it's amazing how often nerves can become indignation and confrontation.

Second: you don't have to decide everything on the spot. Standing in front of a mirror, wearing a half-made pair of trousers, is not always the easiest time to make a decision. Walking away and emailing your choice the next day won't delay anything.

Third, prepare in advance. Obviously reading a lot is helpful, but also:

  • wear similar clothes you like, to compare them with the pieces being fitted;
  • think about what cut and style you want in advance, in fact about every question you might be asked; and
  • bring pictures if that's easier than describing things in words.

Fourth: if you're not sure, ask questions. There's nothing wrong with asking a question, and it may throw up something you hadn't previously realised. 

For example, you may not realise that the first, basted fitting is mostly for the tailor, so he can set the right balance to the garment. The second fitting is more for you - to make decisions about style. 

Fifth and last, if in doubt be open and honest. There's nothing worse than a missed opportunity. 

One reader related an experience where he was slightly disappointed with an initial suit, but considered going back because there seemed to be so much potential. He asked whether this was crazy.

The answer probably depends on whether the tailor can change, and correct those points. It's something you'll really only learn from a conversation with him.

Which is a lot easier to say than do.

Photography: Fitting at Ferdinando Caraceni in Milan, with Nicolleta Caraceni pictured. Shot by Luke Carby

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Kev Fidler

I think one of the most daunting things that someone not experienced in bespoke is the fact that the end product does not yet exist. In a RTW suit etc. you can try on one already made so many of the questions you raise about style, shape and detail can be answered (but not probably altered). One of the attractions of bespoke is you have the opportunity to go along with the process and hopefully achieve what you want, if only you knew how to. Tailors premises are often not the most open and welcoming of places especially if you want to enquire rather than definitely commission. And at many of the prices you want to make very sure that the final product is as near to perfection as possible.
I have noticed that some tailors are offering an initial consultation on lifestyle, clothing preferences and current wardrobe before then recommending style, cloth, even level of make (bespoke, MTO options). It looks an appealing service; do you have any experience or opinion on this, Simon. (I haven’t a clue if the major houses and more traditional tailors do this as matter of course anyway.)



Something that I have started doing with my recent bespoke commissions and which I have found to be pretty useful is to send a summary email to the tailor after the first meeting. I typically go to as much details as possible (and highlight again the ones which are important to me) to make sure that he did not miss anything. That is also a good way to raise new points that you have might forgot to mention or ask for more clarifications. This corroborates to some extent your point on not having to answer right away and come back to the tailor by email after the appointment.


Absolutely and totally agreed that the way it is communicated is key. Would always start by saying how much I appreciated the brainstorming / interaction and just want to summarise my key take-aways and raise a few more points which came across as I was thinking about the commission. So far, the reception I had was always positive. I think for many of the tailors who want their customers as satisfied as possible, they might see value in having an ongoing open conversation rather than limit the exercise to a few scribbles on a paper which will always miss something or some nuances (I am being a by caricatural, I know).

Matt S

I always come up with a list of what I’m looking for in the garment I’m getting when I visit the tailor. I don’t usually show it to the tailor, but it helps me remember everything I want to bring up with the tailor.

John Vesey

Dear Simon—I wanted to let you know that your articles in the Financial Times’s How To Spend It were excellent and I appreciated your insights. Thank you


Simon, as a supplementary or companion piece could you write an article on choosing cloth. It is an important part of the commissioning process but is opaque at the best of times. Tailors often pass the swatch book over the counter but the choice is immense, however the real challenge is how will it look once cut? Colour, weave, pattern, drape, the ability to hold a silhouette and match to wearers character can confuse. Your comments on how to successfully weave your way through these difficulties would be greatly appreciated, especially the dynamic of selecting and agreeing the cloth with the tailor.


Hi Simon,

I enjoyed reading this post as it reminded me on a few instances when I first started commissioning tailoring. However, I wanted to ask whether there is any etiquette for chasing up on commissions?
I ask as I commissioned a summer jacket in April with a new tailor and was quoted a three month turnaround. With five months and counting since the commission, the only time I have been contacted was to be called in for the basted fitting and am a little frustrated that I won’t really be able to wear it until a warm spring day next year. Would it be considered rude if I was to chase a tailor up on his creation??
Maybe in hindsight I should have said that I need it for a particular date!


One of the best tailoring experiences I’ve had was the combination of Greg Lellouche and master tailor Dionisio D’Alise at the No Man Walks Alone / Formasa trunk shows. Greg has great taste and helps advise on style decisions, as well as pointing out any errors, while translating them (literally, into Italian) to the tailor. This arrangement came about organically due to the fact Dionisio doesn’t speak English and is being hosted at the No Man Walks Alone offices, but it could be an interesting model for other tailors to pursue.

Incidentally, I’ve also been to tailors where you see a salesperson in addition to the tailor. Although this works well at the beginning (as the salesperson is usually much more able to give style advice and help with cloth selection) in my experience they seem less willing to make suggestions or criticisms during the subsequent fitting stages. Perhaps an inevitable result of working closely together and the hierarchy in tailoring houses…?

Jack Green

Another element that sometimes arises in the meeting is the tailor subtly steering you towards a style or fit that suits you better than what you had in mind yourself, particularly if you are a creature of habit, or have changed in body shape over the years. How to negotiate this potentially awkward conversation? Often (usually), I have found the tailor’s advice invaluable, but sometimes have felt the need to resist being pushed towards something more modish that simply doesn’t suit me, however fashionable it looks.
However, what I feel the lack of most is a good working vocabulary for the garment under discussion; the component parts and the terms by which different distances and measurements are referred to. How much more confidence I would have if I could use the correct term, rather than awkwardly pointing at ‘this bit here’. And the tailor would feel more confident too, I’m sure.

I wonder Simon, if you could develop a section on the site which offers an ‘illustrated dictionary’ of the most important terms, and meaurements, for suit, shirt and shoes

Ian Franklin

It does seem strange to be reticent when spending £4000 on a suit, but it is difficult to be didactic. As you say, they are the expert at what works, we only know – really? – what we want. I have had coats and trousers made by Richard Anderson (RA) and by Anderson & Sheppard(A&S). I struggled with the gorge on my jackets with RA, but never really confronted the issue with him (sorry, Richard). I do have a very barrel chest, and the A&S cut just worked from the start. So I am there now. Even so, the house style is strong. It’s not easy to ‘fiddle.’ But their suits and jackets look great – but then so do my RA suits, I just prefer the A&S style on me.

facebook_Tony Hughes.10154540072873482

Hello Simon

I’m looking for some advice and have followed the direction to use a comments section rather than email you directly. I trust that’s ok.

My son, who lives just outside London, is getting married in January next year.

As one of our gifts to him we would like to buy him a bespoke shirt for the party that is happening the night before the big day. The setting is a country house hotel and the evening will consist of live music, dancing, causal food and hopefully plenty of fun.

The shirt in question would therefore not be a formal dress shirt but rather a modern shirt that a young man of 26 would wear to such a party with a suitable pair of trousers etc.

Can you advise on who in London you would recommend to make such a shirt?

As an added challenge it can’t be a visiting tailor as we plan to go together to the first fitting and I am travelling to London to be with him on the day of the fitting as I live outside the UK.

Any guidance would be very gratefully received.


facebook_Tony Hughes.10154540072873482

Many thanks Simon, I appreciate the issue of minimum orders. I will make contact with W&S. thanks again

facebook_Tony Hughes.10154540072873482

Hi Simon

I made contact with W&S but unfortunately they can’t take an appointment on a Saturday and this is the only day that works for myself and my son.

Can I ask you for your opinion of Stephen Lachter’s bespoke shirts? as he has said that he will make a off shirt ie no minimum order.

best regards


facebook_Tony Hughes.10154540072873482

sorry that should have been ‘one off’


Simon, I was pleased to see Martin Greenfield mentioned in this post as I have an appointment next weekend with him/them for a light tan summer suit for my wedding in Palm Springs in May. I was, however, wondering if you have any further insight into or opinions on his work that would be useful for someone getting their first bespoke suit?

I know Mr. Greenfield has made suits for a wide variety of brands, and seems to be able to design for all styles and sizes, but any tips would be hugely helpful. For added context I am 5′ 7″, and slightly stocky, so definitely need a suit that can add the illusion of height. I have taken notes from your various posts on how to achieve this (your site has been unbelievably informative), but if you have anything to add that’s specific to this tailor/NYC tailoring that would be greatly appreciated.

Many thanks, Tim.


Not to worry Simon, was worth asking and thanks for replying.

One other thing on which I would love any advice is the type of cloth that would be a smart choice for a light colored summer suit. I’ve seen both cotton and wool fresco mentioned, would you have anything else/more specific to add (in addition to the guides on this site)? It’s likely to be a dry heat in the late 80s-90 degrees for my wedding, but cooling off quickly in the evening.

Thanks Simon, Tim


Greetings Simon,

Thank you so very much for this absolutely superb site. I cannot properly express the degree of enjoyment I have entertained perusing the postings. I am to go to London in the next few weeks to commission a bespoke driving coat from Huntsman. It is my first visit to Saville Row and my first bespoke item and I admit to certainly feeling a degree of trepidation of no undue level.

I was wondering if I might entertain your thoughts on items related to such a jacket that you think indispensable. While I know the traditional Huntsman coat has a longer length I shall ask for something a bit shorter as I drive a vintage sports car quite often and would prefer a shorter length to the coat. Would you recommend a ticket pocket? elbow patches? pockets for my gloves and keys situated in the interior or the exterior of the coat? Also as I drive veritably year round what is a good cloth type to select? If I do select elbow patches what type of color would you select for an Aston Racing Green type coat?

So very sorry for all the questions, but your advice would be most appreciated.

Kindest regards,


Greetings Simon,

Thank you most kindly for your most superb reply. I shall heed your advice and will let you know how things progress. I’m most excited about this project having read all your wonderful articles on the bespoke world.

Many thanks again and kindest regards,


I’ve had a few double breasted suits made by a London tailor and am pleased with the results.

But I’m looking for something with a more obviously aggressive style — a bit of swagger, if you will.

The work of Chittelborough & Morgan, Edward Sexton and Cifonelli look most like what I am seeking now.

How would you describe — in brief — the differences between these three and any particular preference?

Or I am best to stick to my current cutter and somehow encourage him to go outside his standard house style?



Greetings! I’m scheduled to go to New York in a couple weeks for the MTM process that is Martin Greenfield. Although Greenfield MTM suits are presidential/pedestrian compared to the sartorial choices in London and Milan, this is a major personal victory for me. My suit game consists of low end OTR and developing-world MTM debacles whose only redeeming factors are that they each cost less than $200 and are at least 15 years old.

I’m planning on getting two basic suits from Greenfield (2 button charcoal, and 2 button Navy) and I plan to accessorize them cleverly so these will be the only two I need. I’ll be getting waistcoats with both.

Veterans of the Martin Greenfield process, from what I’ve researched, generally indicate that it’s better to go into his Brooklyn shop deferring to his judgement: with ears open, mouth closed, and for heaven sake don’t bring a list. Certainly I want the fit and material to be flattering. I’ll wear the suits for social occasions as well as work.

Simon, given the known Greenfield style/capability, what sartorial details would you ask for from him? Milanese button holes on lapel and sleeves? Highest quality horn buttons? I want to be able to look closely at this suit 10 years from now and still know that I received my money’s worth.

Very grateful Simon!


Wanted to provide a follow up. Took your advice – only had one suit made by the Greenfield group (charcoal single breasted) however I did choose the 3-piece option. I’ve owned the suit for one season and have worn it 2 or 3 times per month. I’ve included the waistcoat for church services, but not at the office yet. Thank you for your advice!


Hi, I’m David, if u want to see me come to Bundu in Nigeria

Philip Poots

Dear Simon,

Firstly let me thank you for your website, it is truly a wealth of information and guidance. I wondered on expanding on this topic about what your opinion would be on not just talking to your tailor but complaining to your tailor about a jacket etc and something about it that did not meet your expectations or that when finished was not entirely acceptable to you.
I’ve just purchased my first bespoke suit and don’t want to alienate my tailor but certainly want to give feedback about certain elements and wondered if you had any advice?